Rest & Relaxation
Rest, Relax, Chill Out, and Reinvegorate your soul
Nature & Wildlife
Expierence the natural beauty of Cape Cod. The Ocean, Wildlife, and Landscapes
Outdoor Activities
World Class Beaches & Sporting Activities
Surfside Inn — Chatham Itinerary
Steps from Lighthouse Beach • Chatham, MA
Day 1: Explore Chatham Village & Coastal Charm
Morning
- Start with a leisurely walk to Chatham Lighthouse Beach. Enjoy the iconic lighthouse and the serene beach atmosphere.
- Visit the Chatham Windmill in Chase Park, a historic 1797 structure offering picturesque views.
Lunch
- Dine at Mac’s Chatham Fish & Lobster Co., known for its fresh seafood and casual ambiance.
Afternoon
- Stroll along Main Street, exploring boutique shops and art galleries.
- Stop by the Eldredge Public Library, a Romanesque Revival building with a spiral staircase and cozy reading nooks.
Evening
- Catch a movie at the Chatham Orpheum Theater, a historic cinema showcasing first-run and independent films.
Day 2: Rainy Day Retreat
Morning
- Visit the Atwood House Museum, a 1752 colonial home with exhibits on Chatham’s history, including a lighthouse turret and WWII displays.
- Explore the Chatham Shark Center, offering interactive exhibits on Great White Shark conservation.
Lunch
- Enjoy a cozy meal at Chatham Squire, a local favorite known for its hearty fare and warm atmosphere.
Afternoon
- Visit the Chatham Railroad Museum, housed in a restored 1887 depot with model trains and historical exhibits.
- Visit Whydah Pirate Museum in Hyannis—home to the only authenticated pirate treasure.
Evening
- Dine at Viera on Main, offering fresh seafood in a charming setting.
Day 3: Beach Day & Scenic Exploration
Morning
- Drive to Nauset Beach in Orleans for a classic Cape Cod beach experience—swimming, sunbathing, or a shoreline walk.
Lunch
- Grab a bite at Liam’s (seasonal), a renowned clam shack near Nauset Beach.
Afternoon
- Explore the Old Colony Rail Trail, a paved path perfect for walking or biking, connecting Harwich to Chatham.
Evening
- Return to Chatham and dine at the Veranda at CBI, offering upscale dining with ocean views.
Day 4: Shopping, Art & Farewell Dinner
Morning
- Browse the shops along Main Street, including antique stores and local boutiques.
Lunch
- Enjoy a meal at Del Mar Bar & Bistro, known for its seafood dishes and elegant setting.
Afternoon
- Relax at Lighthouse Beach, enjoying the beach and amenities.
Evening
- Conclude your trip with a farewell dinner at The Impudent Oyster, savoring their renowned seafood dishes.